1-fluoro-2-(4-methoxyphenethyl)benzene | 1560718-52-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-fluoro-2-(4-methoxyphenethyl)benzene
• 英文别名: 1-Fluoro-2-[2-(4-methoxyphenyl)ethyl]benzene；1-fluoro-2-[2-(4-methoxyphenyl)ethyl]benzene
• CAS: 1560718-52-6
• 化学式: C₁₅H₁₅FO
• 分子量: 230.282
• InChiKey: MTZAQJDGWQRLCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (E)-2-fluoro-4'-methoxystilbene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-fluoro-2-(4-methoxyphenethyl)benzene
  参考文献：
  名称：

  Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators

  摘要：

  A dichloromethane extract of stems and roots of Pholidota chinensis (Orchidaceae) enhanced GABA-induced chloride currents (I-GABA) by 132.75 +/- 36.69% when tested at 100 mu g/mL in a two-micro-electrode voltage clamp assay, on Xenopus laevis oocytes expressing recombinant alpha(1)beta(2)gamma S-2 GABA(A) receptors. By means of an HPLC-based activity profiling approach, the three structurally related stilbenoids coelonin (1), batatasin III (2), and pholidotol D (3) were identified in the active fractions of the extract. Dihydrostilbene 2 enhanced I-GABA by 1512.19 +/- 176.47% at 300 mu M, with an EC50 of 52.51 +/- 16.96 mu M, while compounds 1 and 3 showed much lower activity. The relevance of conformational flexibility for receptor modulation by stilbenoids was confirmed with a series of 13 commercially available stilbenes and their corresponding semisynthetic dihydro derivatives. Dihydrostilbenes showed higher activity in the oocyte assay than their corresponding stilbenes. The dihydro derivatives of tetramethoxy-piceatannol (12) and pterostilbene (20) were the most active among these derivatives, but they showed lower efficiencies than compound 2. Batatasin III (2) showed high efficiency but no significant subunit specificity when tested on the receptor subtypes alpha(1)beta(2)gamma(2)s, alpha(2)beta(2)gamma(2)s, alpha(3)beta(2)gamma(2)s, alpha(4)beta(2)gamma(2)s, alpha(5)beta(2)gamma(2)s, alpha(1)beta(1)gamma(2)s, and alpha(1)beta(3)gamma(2)s. Dihydrostilbenes represent a new scaffold for GABAA receptor modulators. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.008

文献信息

• Nickel-Catalyzed Regiodivergent Reductive Hydroarylation of Styrenes
  作者：Yuli He、Shaolin Zhu、Yuhang Xue、Jian Chen、Peihong Song

  DOI：10.1055/a-1523-3228

  日期：2021.10

  We report a ligand-controlled nickel-catalyzed reductive hydroarylation of styrenes with predictable and controllable regioselectivity. With a diamine ligand, the reaction produces selective linear hydroarylation products. Alternatively, with a chiral PyrOx ligand, branch-selective enantioenriched 1,1-diarylalkane products are obtained. Preliminary mechanistic results are consistent with a reductive

  我们报告了一种配体控制的镍催化苯乙烯还原加氢芳基化，具有可预测和可控的区域选择性。使用二胺配体，该反应产生选择性线性氢化芳基化产物。或者，使用手性 PyrOx 配体，获得分支选择性对映体富集的 1,1-二芳基烷烃产物。初步机械结果与还原 Heck 过程一致。
• Identification of dihydrostilbenes in Pholidota chinensis as a new scaffold for GABAA receptor modulators
  作者：Diana C. Rueda、Angela Schöffmann、Maria De Mieri、Melanie Raith、Evelyn A. Jähne、Steffen Hering、Matthias Hamburger

  DOI：10.1016/j.bmc.2014.01.008

  日期：2014.2

  A dichloromethane extract of stems and roots of Pholidota chinensis (Orchidaceae) enhanced GABA-induced chloride currents (I-GABA) by 132.75 +/- 36.69% when tested at 100 mu g/mL in a two-micro-electrode voltage clamp assay, on Xenopus laevis oocytes expressing recombinant alpha(1)beta(2)gamma S-2 GABA(A) receptors. By means of an HPLC-based activity profiling approach, the three structurally related stilbenoids coelonin (1), batatasin III (2), and pholidotol D (3) were identified in the active fractions of the extract. Dihydrostilbene 2 enhanced I-GABA by 1512.19 +/- 176.47% at 300 mu M, with an EC50 of 52.51 +/- 16.96 mu M, while compounds 1 and 3 showed much lower activity. The relevance of conformational flexibility for receptor modulation by stilbenoids was confirmed with a series of 13 commercially available stilbenes and their corresponding semisynthetic dihydro derivatives. Dihydrostilbenes showed higher activity in the oocyte assay than their corresponding stilbenes. The dihydro derivatives of tetramethoxy-piceatannol (12) and pterostilbene (20) were the most active among these derivatives, but they showed lower efficiencies than compound 2. Batatasin III (2) showed high efficiency but no significant subunit specificity when tested on the receptor subtypes alpha(1)beta(2)gamma(2)s, alpha(2)beta(2)gamma(2)s, alpha(3)beta(2)gamma(2)s, alpha(4)beta(2)gamma(2)s, alpha(5)beta(2)gamma(2)s, alpha(1)beta(1)gamma(2)s, and alpha(1)beta(3)gamma(2)s. Dihydrostilbenes represent a new scaffold for GABAA receptor modulators. (C) 2014 Elsevier Ltd. All rights reserved.